(Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-1-ol

Base Information

• Chemical Name: (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-1-ol
• CAS No.: 198336-12-8
• Molecular Formula: C₃₇H₅₈O₅Si
• Molecular Weight: 610.95

Synonyms:(Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-1-ol

Chemical Property of (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-1-ol

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Technology Process of (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-1-ol

There total 29 articles about (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-1-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

C37H56O5Si (198336-11-7) → (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-2,7,13-trien-1-ol (198336-12-8)

Guidance literature:

With hydrogen; Lindlar's catalyst; In toluene; at 25 ℃; for 0.333333h;

DOI:10.1021/ja973000g

Reference yield: 15.0%

C37H56O5Si (198336-11-7) → (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-2,7,13-trien-1-ol (198336-12-8) + (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-2,7-dien-1-ol

Guidance literature:

With hydrogen; Lindlar catalyst; In toluene; at 25 ℃; for 0.333333h; under 760 Torr;

DOI:10.1021/ja981062g

Reference yield:

(Z)-2-Hydroxymethyl-3-{(1S,2R,6R)-6-isopropyl-2-[(2S,3S)-2-(4-methoxy-benzyloxy)-3-methyl-3-trimethylsilanyloxy-pent-4-ynyl]-3-methyl-cyclohex-3-enyl}-propenal (198336-08-2) → (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-2,7,13-trien-1-ol (198336-12-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / iPr₂NEt / CH₂Cl₂ / 1 h / -78 °C

2: LiHMDS / tetrahydrofuran / 0.17 h / 25 °C

3: NaHCO₃, Dess-Martin periodinane / CH₂Cl₂ / 4 h / 25 °C

4: 94 percent / PPTS / methanol / 0.5 h / 25 °C

5: 75 percent / H₂ / Lindlar cat. / toluene / 0.33 h / 25 °C / 760 Torr

With hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; Lindlar catalyst; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja981062g

upstream raw materials:

C₃₇H₅₆O₅Si

(1S,4S,6S)-4-Isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

(S)-p-mentha-6,8-dien-2-one

(S)-carvone oxide

Downstream raw materials:

Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane

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